The Dexter School opened on Freeman Street in the affluent Cottage Farm neighborhood educating boys through ninth grade.

As Dexter expanded, the school continued the style of the white stucco façade and red terra-cotta roof of the Sears House.

In preparation for the school's move in 1966, the A building, Fiske Hall, and pool and gymnasium were built to the west of the Sears House.

In 1992, the Southfield School was established on the same campus to expand Dexter's educational philosophy to young girls.

Of particular note is the Clay Center for Science and Technology which provided students with classroom opportunities as well as an astronomical observatory.

Dexter Southfield School's curriculum includes arts as painting, wood shop, choir, and much more.

The Varsity Hockey, Lacrosse, Tennis, Football, and Baseball teams have all had many athletes continue their careers at the Division 1 level of NCAA sports.